Nothing conjures up carefree summer days like cycling to the shore on a classic cruiser with a towel and a good book in a bike basket.

While the pristine beauty of Hamptons beaches on the south fork of Long Island is unmatched, splendid discoveries also await along the quiet back roads north and south of Route 27. From the horse farms of Sagaponak to the vineyards of Bridgehampton to the wetlands of Napeaque, there’s no better way to explore the byways — and to beat the local traffic — than to ride a bicycle. Our exclusive Hamptons Riding Guide lays out everything you need to enjoy your summer ride!

Transport Your Bike to the Hamptons

Hampton Jitney Bus & Hampton Ambassador

Get your bike to the beach using the Hampton Jitney and Hampton Ambassador bus services. Bicycles (and surf boards) travel in the cargo hold for $15 each way — in addition to your ticket.

Long Island Railroad

All you need is a one-time $5 permit to transport your bike by rail. Just note that bicycles are accommodated on a first-come, first-served basis and may be excluded during certain high-volume travel times on the Montauk Branch which serves the Hamptons. Bottom line: Check here for the LIRR’s bicycle policy before you roll to the station on a summer weekend.

Suffolk Transit

Travel between the hamlets of the Hamptons using Suffolk County Transit buses. Each coach is equipped with a front-mounted bike rack. Your bike rides free. Find schedules and more information here.

Prettiest sunset in the Hamptons? Take an evening ride to Louse Point in the Springs. Don’t forget your lights!

The store has been fancified since the days when an unknown artist named Jackson Pollack traded paintings for groceries. Now, specialty coffees and cupcakes flank the counter where customers order prepared foods and specialties from the grill.

The East End outpost of the familiar Manhattan food purveyor is located in an historic farmer’s market. Shop for produce and products that are grown (or raised) on the North and South Forks of Long Island.

The ride routes in our guide were created using Map My Ride, a fitness tracking application for GPS-enabled smartphones. Download the app free at this link for pocket navigation and also start recording and sharing your own rides!

RIDES

Before You Ride

The Hamptons draw big crowds on the weekends, and that means traffic. To get the most fun and relaxation out of your ride, follow these tips:

Avoid Route 27Although the shoulders are wide, this main artery through the Hamptons is the least scenic and most congested. Wherever possible, ride your bike on roads north and south of the highway.

Ride to the beach
Although the beaches of the Hamptons are public, access is controlled through seasonal parking permits. Daily parking fees — at limited numbers of beaches that sell them — can be pricey ($40 at Cooper’s Beach in South Hampton). Riding a bicycle is your super power, speeding you past the traffic backups and onto the sandy shores of the beach of your choice.

Get and early start
It’s cooler in the morning, roads are quieter and the beaches are more serene.

Avoid the door zone
There’s on-street parking on the main streets of Hamptons villages, doors may open or cars may pull out unexpectedly. Slow down and watch for brake lights, movement inside a car and other clues that the situation ahead of you may be changing. In certain locales, such as Sag Harbor, cyclists are required to dismount and walk their bicycles on the sidewalks on the main thoroughfare.

Cross safelyWhere possible, cross at an intersection with a traffic light or pedestrian walkway. If you have to cross a main road in the absence of a crosswalk and you feel uncomfortable riding, then dismount, wait for motorists to yield and walk your bike across the street.

Ride single-file
The roads throughout the Hamptons are in generally good condition, but shoulders on non-major roads range from narrow to nonexistent. For safety, ride in single file. Also let those with whom you share the road know your intentions by signaling turns and making eye contact with drivers approaching intersections.

Be alert
Watch out for that motorist who’s too busy dialing his cell phone for a restaurant reservation to pay attention to the road.

Carry lights
Weather at the shore can be changeable, even during daylight when fog can limit visibility. Keep front and rear lights on your bike or in your bag.

Lock up
In keeping with a small-town atmosphere, many people leave bikes unlocked on streets and beaches, but why tempt fate? Secure your bike to hang onto that zen feeling at the beach.

Be courteous
Always give pedestrians the right of way.

Our Favorite Hamptons Bike Rides

Northwest Woods

Quiet and shaded roads of the Northwest Woods in East Hampton offer a serene antidote to the go-go pace of the Hamptons.One of our favorites is a meandering, 12-mile ride beginning in East Hampton Village and ending at the the marina in Sag Harbor. Although there’s usually little traffic in the Northwest Woods, the roads are narrow, so keep to the side and ride single-file. Pause in Sag Harbor for coffee and shopping, or, if you want to extend your ride, pedal to North Haven and catch the South Ferry to Shelter Island.

Sag Harbor Favorites

Life’styleDistinctive apparel and brands for women and men in an airy shop overlooking Sag Harbor’s main thoroughfare.
127 Main Street

ProvisionsThis long-time local favorite for organic and natural foods, also features a juice bar and cafe.
Bay and Division Streets

Sylvester + CompanyCoffee bar with baked goods, chocolate and ice cream, plus beautifully designed home furnishings and accessories in the heart of Sag Harbor.
103 Main St.

Shelter Island

A scenic and relaxing option for a weekend morning ride is Shelter Island, the 8,000-acre island located between the North and South Forks of Eastern Long Island.A $6 round-trip ticket on the South Ferry at North Haven gets you and your bike to this historic summer sailing haven where tree-shaded roads unspool to reveal nature preserves, stately waterfront homes and quaint hamlets. The Ram Island leg of this ride is hilly, so skip it if you want a shorter, more leisurely ride. But if you’re feeling extra-ambitious, the ferry at the northerly end of the Shelter Island is the jumping-off point for the North Fork of Long Island, another great locale to explore on two wheels.

East Hampton to Montauk Point

For more of a challenge, the 40-mile, out-and-back ride from East Hampton through Amagansett to historic Montauk Point is a favorite among weekend cyclists. While most of the Hamptons are flat, a couple of hills await on this ride, so a hybrid or road bike with some gearing options is the best choice. Before you head to the Montauk Lighthouse, the eastern-most point of Long Island’s south fork, pause in the village. Traditionally known for fishing and surfing, Montauk is becoming an increasingly hip destination with enticing boutique hotels, shops and restaurants.

Summer Cycling Events

Explore the “other fork” of Long Island. Ride on mostly flat and quiet back roads dotted with vineyards, horse farms and produce stands, and along the shore of Long Island Sound. Choose 25, 50, 72 or 100 mile routes.

Now in its 21st year, the Tour of the Hamptons begins in Southampton and wends east toward Montauk on a mostly flat course. Route options, which lead riders through historic hamlets, estate districts and farmland, include 25, 50, 70 and 100 miles, plus two 25-mile guided rides.